Regioselective 1,2-Alkylboration of Benzylidenecyclopropanes: Access to Csp3-Enriched Cyclopropyl Boronic Esters

被引：2

作者：

Mondal, Pinku Prasad ^{[1
]}

Nair, Anagha Veluthanath ^{[1
]}

Sasidaran, Megha ^{[2
]}

Chungath, Alvin Antony ^{[1
]}

Suman, Satya Prakash ^{[1
]}

Kuniyil, Rositha ^{[2
]}

Sahoo, Basudev ^{[1
]}

机构：

[1] Indian Inst Sci Educ & Res Thiruvananthapuram, Sch Chem, Thiruvananthapuram 695551, Kerala, India

[2] Indian Inst Technol Palakkad, Dept Chem, Palakkad 678623, Kerala, India

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 07期

关键词：

SECONDARY; TERTIARY;

D O I：

10.1021/acs.orglett.4c00087

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe a novel, regioselective alkylboration of versatile (hetero)benzylidenecyclopropanes with beta-H-containing alkyl iodides and bis(pinacolato)diboron enabled by copper catalysis. This three-component method allows for consecutive B-Csp(3) and Csp(3)-Csp(3) bond formation to access Csp(3)-enriched diverse tertiary cyclopropyl boronic esters with broad functionality tolerance, and the so-formed C-B bond is amenable to further structural diversification. Radical clock experiment, Hammett analysis, and DFT calculation suggest a mechanism of polar, rather than radical manifold, and S(N)2-type C-C bond formation was found to be the rate-limiting step instead of migratory alkene insertion.

引用

页码：1458 / 1462

页数：5

共 10 条

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Mondal, Pinku Prasad
Nair, Anagha Veluthanath
Sasidaran, Megha
Chungath, Alvin Antony
Suman, Satya Prakash
Kuniyil, Rositha
Sahoo, Basudev
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